This invention concerns a process for the production of valuable chemical intermediates by the cross dimerization of two compounds containing carbon-carbon double bonds. Specifically provided is a process for the production of methyl 4-pentenoate (M4P).
It is generally known to use nickel catalysts in the dimerization, oligomerization, and polymerization of olefins.
The present invention, however, provides a novel process which is a highly selective route to methyl 4-pentenoate, an intermediate in the manufacture of adipic acid, via cross-dimerization. Adipic acid is one of the starting materials in the manufacture of nylon 6,6.
G. Wilke et al., Angew. Chem. Int. Ed. Engl. (1988), 27, 185, report the polymerization of ethylene to linear polyethylene by a nickel catalyst.
G. Wilke et al., Angew. Chem. Int. Ed. Engl. (1988), 27, 185, present a general review on Ni-catalyzed dimerization, oligomerization and polymerization of olefins.
G. Wilke et al., Angew. Chem. Int Ed. Engl. (1966), 5, 151, and 897, and Angew. Chem., Int. Ed. Engl. (1966), 5, 582, disclose general procedures for preparing allyl-nickel-halide and allyl-nickel-methyl complexes. No detailed experimental procedures were reported.
Laufenberg (U.S. Pat. No. 5,324,847) discloses methods of preparing ethylene adducts of polyunsaturated 18-22 carbon fatty acids or alkyl esters in the presence of Ru, Rh, Pd, Ir, and Pt-containing catalysts.
Drent (U.S. Pat. No. 4,692,548) discloses methods of reacting acrylate esters and ethene using Ru or Pd compounds along with Ag or Cu salts.